1. Field of the Invention
The present invention relates to optically active binaphthol monophosphoric acid derivatives, optically active binaphthol monophosphate derivatives and their use. The optically active binaphthol monophosphate acid derivatives of the present invention are important as in intermediates for synthesis of various catalysts for asymmetric synthesis, and the binaphthol monophosphate derivatives derived therefrom have high reactivity in various asymmetric synthetic reactions and provide reaction products having a high optical purity. Pyran compounds obtained by the method of the present invention are useful compounds as intermediates for synthesis of pharmaceutical and agricultural chemicals.
2. Discussion of Background
The binaphthol monophosphoric acid derivatives of the present invention and the binaphthol monophosphate derivatives derived therefrom, have not been conventionally known, and they are novel compounds.
As one example of reactions to which the catalyst for asymmetric synthesis of the present invention is applicable, Diels-Alder cyclization reaction will be explained below.
As the Diels-Alder cyclization reaction, many reactions of a diene with an olefin in the presence or absence of a Lewis acid catalyst such as aluminum chloride, have been known for a long time.
As an asymmetric Diels-Alder cyclization reaction, e.g. a reaction of acryl-1,3-oxazolidin-2-one with cyclopentadiene has been known (Shu Kobayashi et al, J. Org. Chem., 1994, 59, 3758).
As an asymmetric hetero Diels-Alder cyclization reaction, e.g. a reaction of a benzaldehyde with a diene has been known (Hisashi Yamamoto et al, J. Am. Chem. 1988, 110, 310).
However, with respect to the conventional asymmetric Diels-Alder cyclization reactions and asymmetric hetero Diels-Alder cyclization reactions, the reaction temperature is as low as at most -20.degree. C. in all known reactions, whereby these reactions are not satisfactory as an industrial production method, although a reaction product having a high optical purity may be obtained in some of these reactions.